Beta-acetylalkylene-tetraalkyldiamins.



UNTTED @TATES PAEFENT @IFFT CE.

GEDRG- MERLING AND OTTO OHRZESCINSKI, OF ELBERFELD, AND HUGO KOHLER, OF

LEVERKUSEN, NEAR COLOGNE, GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM. FRIEDB. BAYER & 00., 0F ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

Limit 754i.

No Drawing.

To all whom it may concern Be it known that we, Guone MERLING, OTTO CHRZEsoINsKI, and HUGO KoHLER, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberfeld, Elberfeld, and Leverkus'en, near Cologneon-the-Rhine, Germany, havev invented new and useful Improvements in Beta-Acetylalkylene-Tetra-alkyldiamins, of which the following is a specification.

The present invention concerns the pro duetion of the hitherto unknown keto compounds of the formula:

h 00 C /CHN(R)2 r om-mung (R==hydrogen or alkyl, R=alkyl) fully the following examples are given, the

parts being by weight:

Example 1-Pr0ductt'0n of beja-acetylhimethyzenetetraethg/Zdiamin from tetraethg Z- tlz'amz'nomethane and acetone.750 parts of aqueous formaldehyde (40 per cent.) are gradually dropped into 3,245 parts of equeous diethylamin solution (45 per cent.) which is being stirred and cooled and 2,000 parts of acetone, 400 parts of baryta water (saturated at ordinary temperature) and 500 parts of water are then added. After days heating from to C. bicarbonato is added to the brown solution in. order to remove the baryta. Barium carbonate is removed by filtration. The oil is separated with potash from the filtrate and dried over potash. The excess of acetone is removed by distillation in vacuo and the remaining mixture of bases is decomposed Specification of Letters Patent.

Application filed .Tune 5, 1913.

' BETA ACETYLALKYLENE TETRAALKYLDIAMINS.

Patented June 30, 1914.

Serial No. .'?71,952.

by a fractional distillation in mono to betaacetyltrime'thylenetetraethyldiamin, tions from about 90-110 C. 7-8 mm). This base represents a colorless and odorless oil with a little yellow coloration. boiling at 95l00 C. (7 to 8 mm).

Errrzmple .@Pr0rlucti0n 0f beta-0cmlzcctg lmczfhyltrimethylenetctracthylrliamin CH,.-N(C2H5,l2

from tetmezf/zg lrliom-inomefiz(me and methylethg Z/aet0ne.-292 parts of an aqueous-(liethylamin solution per cent.) are gradually dropped into 75 parts of aqueous formaldehyde '(40 per cent.) while well stirred and cooled. This mixture forming two layers, is miXcd with 210 parts of methylethylkctone and boiled on the reflux condenser for so long a time until a test portion after acidulation with acetic acid is not any more rendered turbid by a solution of anilin acetate which requires several hours. The solution is then dehydrated with potash and worked up in the same manner as described in Example 1 whereby an analogous result is obtained. The new beta beta acetyl methyltrimethylenetetra ethyldiamin of the formula:

Ca -moles 'C. (78 mm.) being soluble in water.

l/Ve elaim 1. As new products the beta-acetylalkyl- (fracenetetraalkyldiamins, which are colorless and odorless oils being soluble in water, substantially as described.

2. As new products the beta-acetylalkylenetetraethyldiamins, which are colorless and odorless oils being soluble in water, substantially as described.

3. As new products the beta-acetyltrimethylenetetraalkyldiamins, which are colorless and odorless oils being soluble in water,

substantially as described.

4. As neW product the beta-acetyltrimethylenetetraethyldiamin of the formula Which is. colorless and odorless oil with a little yellow coloration boiling at 95-100 C. (78 mm.) being soluble in Water and be ing split up by heating it With dilute sul- 10 :furio acid into diethylamin and beta-acetylalkyldiethylmnin, substantially as described.

In testimony whereof We have hereunto set our hands 1n the presenoe of two subsonblng wltnesses.

GEORG MERLING. [L.S.] OTTO CHRZESGINSKI. 11.5. HUGO KOHLEB. s]

lVit-nesses:

HELEN NUFER, ALBERT NUFER. 

